Bill: Every girl I meet wants a monogamous relationship from the get-go, but I'm 26 and I don't want to settle down or anything yet. I like to play the field. I don't want to be a dick about it, but I also don't want to lie about my intentions. Why can't girls just have open relationships too? Basically the question is: When am I obligated to tell her that this is not going to be a monogamous relationship?
Craig - you’re too old to be a piece of shit. You know what you’re doing. You’re leading these women on, acting like you’re looking for a relationship and then after you’ve banged ‘em a couple of times, you drop the bomb. “I’m not looking for a girlfriend right now…” That’s basically the dating version of what Bill Belichick did to the New York Jets back when they thought he was gonna be their coach. So from here on out, you have to have that conversation from the second you meet someone. Just say what you’re looking for and let the chips fall where they may.
If I had to guess, I’d say you’re afraid that if you state that you’re just looking for a physical relationship, women are going to head for the hills. The reality is, some will and some won’t. A lot more won’t than you think. At 26 there are plenty of women that are looking for the same thing you are, so just put it out there, then honor that statement by keeping your word: Don’t start doing boyfriend shit with them. Hook up and then leave: Even if you say you aren’t looking for a relationship upfront, if you start going to movies or hanging out watching TV, you’re sending mixed signals. Swing by once every two to three weeks. Stick and move son! Good luck!
How do I ask my new girlfriend to try anal? Every time I wanna do it I feel like a perv.
Adrian –My gut says don’t ask her. Dump her and then go bang some girl you don’t care about in the ass. As of right now, you’re too uncomfortable to pull this off. So let’s try and work through this. I think the real question here is: Why do you feel like a perv when you think about asking your girlfriend to try anal? Is it because it’s widely considered a filthy act done by dirty whores? OF COURSE! In a perfect world, there would be no judgment. And if two people wanted to try something, and they were both into it, it would be no big deal. But we don’t live in a perfect world, so if you’re going to make this dream a reality, you have to create that perfect, non-judgmental world in your bedroom. I don’t know how far you’ve gone with your girl, but it seems that anal would require a Neil Armstrong voice over. So start slow - you’re going to have to work your way up to this act. Start by finding out what your girl is into but has never tried, then try it. Then don’t judge her. Then tell her something you want to try. Then try that. Then repeat the process over and over, gradually working your way up the pervert ladder until the idea of sticking your dick in her bum will be as normal as asking her to pass the salt. Good luck!
Got a problem that only a brutally honest answer from Bill will solve? Email it to firstname.lastname@example.org with "Bill Burr" in the subject line.